| | I would say that Rand's biggest "mistake", beyond any errors in her personal life, might have been her refusal to debate her philosophy in public, to delve into the prevailing ideas in the field and take them apart philosophically. She constructed a system that she thought would appear so obviously true that no argument could hold against it, but she didn't bother to defend it from those critics who did address it seriously, any more than she bothered to write a fully researched intellectual critique of any of her major philosophical opponents (i.e. Kant). Had she done so even a couple of times, she might be taken more seriously by the intellectual community - college students would study her works in class, and be led to think about the problems of the world in a different light than most of the contemporary liberal arts shine. If you think this wouldn't have worked, look at Robert Nozick - a contrarian thinker if ever there was one, and as hardcore a minimal-state libertarian as Rand (though from different premises), but still one of the most respected philosophers of the late 20th century.
That said, I might regroup all this argument into an "I wish she had..." category, since I can't honestly condemn her for focusing more of her intellectual energies on writing for the general public; she certainly had a great impact that way. I merely think the impact would be deeper, more a part of our cultural core as it were, if her ideas could penetrate into the heart of academia and make more of the thinkers of the future take notice.
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